Like many children of privilege and insanity, Saadi never had to learn the difference between boyhood dreams and reality. So if he wanted to be a star soccer player, but wasn't particular good at soccer, it was going to happen anyway. At the ripe old age of 27, and with no professional experience, he managed to land a starting striker role for Al-Ahly Tripoli, the most storied and successful of Libyan teams. When they failed to win a championship, Gaddafi landed a transfer to the team who did — starting every game and winning two titles with Al-Ittihad Tripoli. (Here he is scoring from a free kick and removing his shirt.)

But the Libyan league was too small a pond for Saadi. He had always wanted to play in Italy, so he made it happen in a matter of months. And all it took was years of hard work his family owning a large stake in Juventus. But Juventus has a history, and wouldn't lower itself to a stunt signing. Enter Perugia and chairman Luciano Gaucci, who will lower himself to anything.

His Perugia career was tragicomic. A public battle ensued between owner and manager, who refused to play Gaddafi because he was terrible. After months on the bench, something had to give. It turned out to be Saadi, who failed a drug test for the steroid nandrolone. His excuse was the medicine for a chronic back injury, and his team threatened to boycott Serie A. Someone, somewhere, with lots of oil money, pulled some strings, and Saadi's mandatory 2-year suspension was reduced to three months.

Gaddafi's time finally came in May 2004, as Perugia faced off against Juventus, needing a win to avoid relegation. Up 1-0 in the 75th minute, manager Serse Cosmi called for a sub, presumably to add an extra defender. It was the obvious strategy. Instead, Cosmi subbed in Saadi Gaddafi, a striker. Cosmi tried to justify the move:

"Gaddafi came on because he is a player and not because any one of us wanted to go into history as the one who first played the son of a head of state in the Italian championship."

Gaddafi did not touch the ball. Perugia held on to win, but Cosmi was fired. Gaddafi spent the next year on the bench without getting in a match, and after the 2004-2005 season, Perugia went bankrupt and Luciano Gaucci fled to the Dominican Republic to avoid jail time.

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Gaddafi signed with Udinese, and got one more taste of glory, appearing for 11 minutes in a meaningless late-season match. He recorded his first and only shot in Serie A, and then never played again.